anthracen-9-ylmethyl (2S)-2-hydroxy-3-methylbutanoate | 200392-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthracen-9-ylmethyl (2S)-2-hydroxy-3-methylbutanoate
• CAS: 200392-00-3
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: NGBTVFNIWRTKIE-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-anthroyl)-[1,2,4]triazole 、 anthracen-9-ylmethyl (2S)-2-hydroxy-3-methylbutanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以68%的产率得到9-anthrylmethyl (S)-2-(2-anthroyloxy)-3-methylbutanoate
  参考文献：
  名称：

  CD激子手性法的新应用。含有羧酸基团的有机化合物的立体化学分配

  摘要：

  描述了CD激子手性方法对含有羧酸基团的有机化合物的立体化学分配。使用发色性的2-萘甲酸酯或2-邻苯二甲酸酯和9-蒽甲基的组合，可以从单次CD测量推论出α-和β-羟基羧酸的绝对立体化学。此外，如用环状和酰基二羧酸所证明的那样，空间位阻的羧基与2-萘酚的直接酯化也允许 通过 CD光谱进行立体化学分配 。

  DOI：

  10.1007/s00706-004-0277-4
• 作为产物：
  描述：

  anthracen-9-ylmethylene-hydrazine 在 manganese(IV) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 anthracen-9-ylmethyl (2S)-2-hydroxy-3-methylbutanoate
  参考文献：
  名称：

  Absolute Configurational Assignment of Acyclic Hydroxy Carboxylic Acids:  A New Strategy in Exciton-Coupled Circular Dichroism

  摘要：

  A new strategy in exciton-coupled circular dichroism (ECCD) is described for the configurational assignment of alpha-hydroxy carboxylic acids. Using 9-anthryldiazomethane (4), carboxyl groups can be selectively derivatized with a chromophore suitable for exciton coupling. In combination with the 2-naphthoate chromophore linked to the alpha-hydroxy group, the absolute stereochemistry of alpha-hydroxy carboxylic acids can be easily deduced from a single CD measurement. The usefulness of the new method is demonstrated with a series of alpha-hydroxy acids with different side chains. The developed microscale method is also useful for chiral amino acids and natural products containing carboxyl groups or similar structural units.

  DOI：

  10.1021/jo971589w

文献信息

• New Applications of the CD Exciton Chirality Method. Stereochemical Assignment of Organic Compounds Containing Carboxylic Acid Groups
  作者：Anne Fischbeck、Nana Bartke、Hans-Ulrich Humpf

  DOI：10.1007/s00706-004-0277-4

  日期：2005.3

  CD exciton chirality methods are described for the stereochemical assignment of organic compounds containing carboxylic acid groups. Using the chromophoric combination 2-naphthoate or 2-anthroate and 9-anthrylmethyl group the absolute stereochemistry of α- and β-hydroxy carboxylic acids can be deduced from a single CD measurement. Furthermore, as demonstrated with cyclic and acylic dicarboxylic acids

  描述了CD激子手性方法对含有羧酸基团的有机化合物的立体化学分配。使用发色性的2-萘甲酸酯或2-邻苯二甲酸酯和9-蒽甲基的组合，可以从单次CD测量推论出α-和β-羟基羧酸的绝对立体化学。此外，如用环状和酰基二羧酸所证明的那样，空间位阻的羧基与2-萘酚的直接酯化也允许 通过 CD光谱进行立体化学分配 。
• Absolute Configurational Assignment of Acyclic Hydroxy Carboxylic Acids:  A New Strategy in Exciton-Coupled Circular Dichroism
  作者：Katja Hör、Olaf Gimple、Peter Schreier、Hans-Ulrich Humpf

  DOI：10.1021/jo971589w

  日期：1998.1.1

  A new strategy in exciton-coupled circular dichroism (ECCD) is described for the configurational assignment of alpha-hydroxy carboxylic acids. Using 9-anthryldiazomethane (4), carboxyl groups can be selectively derivatized with a chromophore suitable for exciton coupling. In combination with the 2-naphthoate chromophore linked to the alpha-hydroxy group, the absolute stereochemistry of alpha-hydroxy carboxylic acids can be easily deduced from a single CD measurement. The usefulness of the new method is demonstrated with a series of alpha-hydroxy acids with different side chains. The developed microscale method is also useful for chiral amino acids and natural products containing carboxyl groups or similar structural units.